Glycosidic inhibitors of melanogenesis from leaves of Passiflora edulis.

Abstract

A new flavonoid glycoside, chrysin 6-C-β-rutinoside (chrysin α-L-rhamnopyranosyl-(1→6)-C-β-glucopyranoside; 2), and two new triterpene glycosides, (31R)-31-O-methylpassiflorine (7) and (31S)-31-O-methylpassiflorine (8), along with 14 known glycosides, including three flavonoid glycosides, 1, 3, and 4, six triterpene glycosides, 5, 6, and 9-12, three cyano glycosides, 13-15, and two other glycosides, 16 and 17, were isolated from a MeOH extract of the leaves of Passiflora edulis (passion flower; Passifloraceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of compounds 1-17 against the melanogenesis in the B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), three compounds, isoorientin (1), 2, and (6S,9R)-roseoside (17), exhibited inhibitory effects with 37.3-47.2% reduction of melanin content with no, or almost no, toxicity to the cells (90.8-100.2% cell viability) at 100 μM. Western blot analysis showed that compound 2 reduced the protein levels of MITF, TRP-1, and tyrosinase, in a concentration-dependent manner while exerted almost no influence on the level of TRP-2, suggesting that this compound inhibits melanogenesis on the α-MSH-stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of TRP-1 and tyrosinase. In addition, compounds 1-17 were evaluated for their inhibitory effects against the EpsteinBarr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells.

• Authors: Jie Zhang, Ryosuke Koike, Ayako Yamamoto, Motohiko Ukiya, Makoto Fukatsu, Norihiro Banno, Motofumi Miura, Shigeyasu Motohashi, Harukuni Tokuda, Toshihiro Akihisa
• Journal: Chemistry & biodiversity (Chem Biodivers) Vol. 10 Issue 10 Pg. 1851-65 (Oct 2013) ISSN: 1612-1880 [Electronic] Switzerland
• PMID: 24130028 (Publication Type: Journal Article)
• Copyright: Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich.

Chemical References

• Antigens, Viral
• Disaccharides
• Epstein-Barr virus early antigen
• Flavones
• Flavonoids
• Glycosides
• Interferon Type I
• Melanins
• Pregnancy Proteins
• Saponins
• Triterpenes
• chrysin 6-C-rutinoside
• interferon tau
• alpha-MSH
• Monophenol Monooxygenase
• Methanol

Topics

• Animals
• Antigens, Viral (chemistry, metabolism)
• Cell Differentiation (drug effects)
• Cell Line, Tumor
• Cell Survival (drug effects)
• Disaccharides (chemistry, isolation & purification, pharmacology)
• Flavones (chemistry, isolation & purification, pharmacology)
• Flavonoids (chemistry)
• Gene Expression Regulation (drug effects)
• Glycosides (chemistry, isolation & purification, pharmacology, toxicity)
• Humans
• Interferon Type I (genetics)
• Melanins (antagonists & inhibitors, biosynthesis)
• Methanol (chemistry)
• Mice
• Monophenol Monooxygenase (genetics)
• Passiflora (chemistry, metabolism)
• Plant Leaves (chemistry, metabolism)
• Pregnancy Proteins (genetics)
• Saponins (chemistry, isolation & purification, pharmacology)
• Stereoisomerism
• Triterpenes (chemistry)
• alpha-MSH (metabolism)